Life is all about making choices, and often times, it’s difficult to know if we’re making the best choice—or even the right choice. In this article, I’m going to provide you with my ten favorite songs about choices, ranging from rock to rap to pop music.
Should I Stay or Should I Go? By The Clash
“Should I Stay or Should I Go?” can be interpreted in many ways. On the surface, the lyrics seem to suggest that it is written from the vantage of someone in a casual relationship without clearly defined boundaries. They’re cool to “be here ‘til the end of time,” if that’s what their presumed paramour wants, but “this indecision” is uncomfortable and causes the speaker to question if it’s worth the effort.
The vocals and guitars take turns in the forefront of the song and are absolutely infectious. It is impossible to hear this one without singing along.
Papa Don’t Preach by Madonna
Madonna was the undisputed pop queen of the 1980s with a number of hits receiving regular radio rotation. Although much of her music is lighthearted and fun like “Material Girl,” “Papa Don’t Preach” took a more serious tone, sung from the perspective of a fearful expecting mother as she entreats her father for his support and advice.
Her father does not approve of her lover and her friends are pressuring her to get an abortion. She urges her father not to lecture her or “preach” about the grave mistake he believes she is making. She’s keeping her baby and she’s asking her father to look past his own preconceptions to be present for her during her time of need.
You don’t have to be in such a specific predicament to understand the gravitas of the conflict present here. Most of us have had to make difficult decisions and have had to ask our loved ones for their support even when it is not in line with what they feel is right.
You Belong with Me by Taylor Swift
T Swift is widely known for her empowering anthems, heartfelt love tracks, and breakup songs.
“You Belong with Me” touches on many of these tropes, and is one of the best songs about decisions ever released. Taylor’s character is a self-identified geeky girl who yearns for a romantic relationship with her close male friend. Unfortunately, he’s attached to a stereotypical “cheer captain” archetype.
Taylor doesn’t think her friend is happy with this short-skirt wearing teenager, and so she professes her love for him in this song and asks him to reconsider his choice. The song does not reveal whether or not he chooses Taylor in the end, but the music video gives us our answer as our blonde female protagonist, played by Taylor, wins over the boy from the other girl, also played by Taylor but with brown hair, at their prom.
Jumper by Third Eye Blind
Stephan Jenkins’ lyrics are absolute poetry, and the eponymous 1997 debut of Third Eye Blind is a masterpiece. Among the many singles pulled from that album is “Jumper,” a slow building acoustic ballad sung to a person standing on the edge of a ledge intending to jump to their death. The speaker pleads with the jumper to reconsider and choose life by stepping down and putting the past away to move forward.
The lyrical content augments an already beautifully crafted musical arrangement—Jenkins twangy, raspy vocals, an infectiously addictive acoustic melody leading into a quiet breakdown that builds slowly towards an exhilarating crescendo, and just as the music reaches its peak the band cuts out and Jenkins shouts, “Can you put the past away?” Chills. Every time.
Paradise by the Dashboard Light by Meat Loaf
Ain’t no doubt about it; Meat Loaf was an impressive vocal powerhouse. His talents are showcased on classic tune “Paradise by the Dashboard Light” which, in simple terms, is about two teenagers fooling around in a car. The lyrics are dripping with vivid imagery and sexuality including a baseball broadcast, performed by Phil Rizzuto, that describes the action euphemistically.
The song really shines after the baseball breakdown as guest singer Ellen Foley halts the action abruptly and asks Meat Loaf if he loves her. He tries to buy time, but she’s gotta know right now! Meat Loaf and Foley overlap in an iconic dual vocal section, but she won’t back down.
Pressured to make a choice, Meat Loaf does what many teenage boys would do and provides a resounding yes. The song becomes a cautionary tale as Meat Loaf’s character will “never break his promise or forget his vow” but now is “praying for the end of time” so he could get away from Foley.
“Paradise by the Dashboard Light” is a classic tune, and we highly recommend this one for your next karaoke night!
Molly by Lil Dicky
Those who know Lil Dicky are probably most acquainted with his humorous raps like “Professional Rapper” or “Freaky Friday,” a song where he wakes up as Chris Brown and lives a day in his life.
“Molly” is uncharacteristically serious, written for Dicky’s ex-girlfriend who he was dating when his music career started ramping up. While he loved her, the two decided that the relationship could not withstand Dicky’s imminent public lifestyle. He reluctantly chooses to let her go.
The rhymes on “Molly” are topnotch, featuring his trademark rapid fire delivery and internal rhyme schemes to keep things fresh. The backing track is somber and subdued to reflect the pain and heartache expressed in the lyrics, only opening up with an anthemic chorus sung by alternative pop icon Brendan Urie.
Throw in a music video cameo from Internet funnyman Logan Paul, and this song is cemented in as one of Lil Dicky’s best.
Guilty Conscience by Eminem featuring Dr. Dre
Back in 1999, when Eminem was only known as Dr. Dre’s protégé, the two released a single sung as the proverbial angel and devil on the shoulders of three separate individuals as they consider making serious decisions.
Dr. Dre plays the role of the angel, advocating for ethical conduct and considering each variable thoroughly, whereas Slim Shady pressured the characters in the story towards impulse, violence, and criminal behavior.
“Guilty Conscience” remains compositionally impressive and artistically ambitious. While the song’s content is dark and serious, Eminem inserts his twisted humor in the final verse when, instead of focusing on persuasive argument, he pivots and personally insults Dr. Dre, eventually resulting in the two reaching an agreement about the final choice.
Rolling Stone consider it to be Eminem’s 14th best song.
Swing by Taking Back Sunday
While Taking Back Sunday is most known for their early work during the 2000s emo alternative movement, “Swing” is a gem from 2009’s New Again that deals greatly with choices and indecision. From the upbeat tempo, soaring guitar leads, thumping bassline, and characteristic dual vocals and repeating refrains, “Swing” is an auditory delight that you’ll be singing to yourself all day.
The lyrics are sung from the perspective of a spurned lover who “never had a choice” in the ending of a passionate fling, and now it’s only a matter of time before they become just a memory. The speaker urges their former lover to reconsider and choose “ passion over consequence.” Singer Adam Lazzara uses a recurring symbol of a lover sitting on a fence, and it is clear the speaker believes that there is still hope for change.
The General by Dispatch
“The General” is a folk indie novella that tells the tale of an old grizzled general on the eve of a great battle when suddenly he decides that the “fight is not worth fighting.” In light of his epiphany, he summons his troops and orders them to go home, imploring them to live their lives to the fullest. Despite this instruction, the general then chooses to honor his duty and ride into battle alone.
This powerful message reminds listeners that life is fleeting and that we must take every opportunity to seize the day. Dispatch uses full-bodied acoustic guitar chords, a funky walking bassline, and delicious vocal chorus harmonies to craft this unforgettable masterpiece.
Two Princes by Spin Doctors
If you grew up in the 90s, you definitely heard this 1991 treasure by the Spin Doctors, even if you didn’t know it’s actually titled “Two Princes.”
In this classic 90s jam, singer Chris Barron sets the scene of two princes vying for the love of a lady. Although her father would approve of the princes and they would provide her with lavish luxuries, Barron asks her to choose him instead. He “ain’t got no future or family tree” but he loves her and says he knows how to treat her right.
Kicking things off with a snare drum pitter-patter and wailing guitar lead, this tune is an absolute earwig featuring a relentlessly catchy bridge section with the iconic refrain “just go ahead now.” This song was literally everywhere in 1991 and remains a solid hit even today.
At some point in our lives, whether it’s related to work or a relationship, we all are faced with tough decisions. That’s what makes songs about choices so compelling to listen to, because an artist can paint a tough circumstance in vivid detail in under 4 minutes—and we’re riveted the entire time.
Hopefully, you not only will find a couple songs on this list relatable or fun, but ones you can add to your personal playlist, as well.